Development of a New Method for the Ring of Pyrrolizine
Abstract
Pirolizin bileşiklerinin doğadaki bolluğu ve göstermiş olduğu önemli biyolojik aktiviteler nedeniyle sentez kimyası için de oldukça önemli bileşiklerdir. Bu heterosiklik yapıların sentezi için farklı sentetik metotlar kullanılmakla birlikte bu yapılar doğal ürün olarak çeşitli bitkilerden de elde edilebilmektedirler. Pirolizin iskeleti içeren türevlerin elde edilmesi için ortaya konacak metodolojiler oldukça önemsenmektedir. Bunun nedeni de bu konuda kısıtlı sayıda çalışmanın olmasıdır. Bu tez çalışmasında, diketon bileşikleri Claisen Schmidt Kondenzasyonu reaksiyonu ile sentezlenmiştir. Diketon bileşikleri okzalil klorür ile farklı metotlarla lakton türevlerinin sentezinde kullanılmıştır. Sentezlenen lakton türevlerinin kuru benzen ortamında pirol ile reaksiyonu sonucu tek kademede ve katalizör olmadan 2 saat içerisinde oda sıcaklığında literatürde bilinmeyen 7 farklı pirolizin türevinin sentezi gerçekleştirilmiştir. Bu pirolizin türevlerinde asetil, naftil, tiyofen, bifenil, triflorometil, fenil, etoksi gibi önemli fonksiyonel gruplar bulunmaktadır. Sentezlenen pirolizin türevlerinin yapıları 1H ve 13C NMR, COSY, HMQC, HMBC ve LC-MS gibi spektroskopik yöntemler ile karakterize edilmiştir.
Pyrrolizines are very important for synthetic chemistry due to the abundance of pyrrolizine compounds in nature and the important biological activities which they show. Although different synthetic methods are used for the synthesis of these heterocyclic structures, they can also be obtained from various plants as natural products. Methodologies for obtaining pyrrolizine containing derivatives are highly demanded. That is why the subject of this thesis is to synthesis unknown pyrrolizines. In this thesis, diketon compounds were synthesized by Claisen-schmidt condensation reaction. Diketone compounds have been used in the synthesis of lactone derivaties by different methods. As a result of the reaction of the synthesized lactone derivaties with pyrrole in dry benzene medium, synthesis of 7 different pyrrolizine derivaties was performed in one step and without catalyst in 2 hours at room temprature. These pyrrolizine derivatives contain important functional groups such as acetyl, naphthyl, thiophene, biphenyl, trifluoromethyl, phenyl, ethoxy. The structures of synthesized pyyrrolizine derivatives were characterized by 1H and 13C NMR, COSY, HMQC, HMBC and LC-MS spectroscopic methods.
Pyrrolizines are very important for synthetic chemistry due to the abundance of pyrrolizine compounds in nature and the important biological activities which they show. Although different synthetic methods are used for the synthesis of these heterocyclic structures, they can also be obtained from various plants as natural products. Methodologies for obtaining pyrrolizine containing derivatives are highly demanded. That is why the subject of this thesis is to synthesis unknown pyrrolizines. In this thesis, diketon compounds were synthesized by Claisen-schmidt condensation reaction. Diketone compounds have been used in the synthesis of lactone derivaties by different methods. As a result of the reaction of the synthesized lactone derivaties with pyrrole in dry benzene medium, synthesis of 7 different pyrrolizine derivaties was performed in one step and without catalyst in 2 hours at room temprature. These pyrrolizine derivatives contain important functional groups such as acetyl, naphthyl, thiophene, biphenyl, trifluoromethyl, phenyl, ethoxy. The structures of synthesized pyyrrolizine derivatives were characterized by 1H and 13C NMR, COSY, HMQC, HMBC and LC-MS spectroscopic methods.
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Kimya, Chemistry
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